


100 Dicks and Dean

by ashandcas (ashriddle4)



Category: Supernatural
Genre: 7x12 coda, Anal Fingering, Anal Sex, Angry Sex, BDSM, Blow Job, Demon!Dean, Dirty Talk, Fingering, Handcuffs, M/M, Masturbation, Mentions of homophobia, Rough Sex, Season/Series 10, Semi-Canonical Character, Semi-Public Sex, Sex Toys, Spanking, Sub!Dean, There will be a destiel chapter later, delusional!crowley, dildo, it's just mentions of Dean/Castiel rn, sexist terms, tags will update, will be a collection of dean with a lot of different men
Language: English
Status: In-Progress
Published: 2015-03-05
Updated: 2015-03-17
Packaged: 2018-03-16 11:26:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 6,553
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3486497
Author URL: https://archiveofourown.org/users/ashriddle4/pseuds/ashandcas
Summary: <blockquote class="userstuff">
              <p>This is a collection of stories of different characters (original and canonical) which form a portion of Dean's sexual experience. Lots of smut, lots of feeling.</p>
            </blockquote>





	1. Dean/WWII Soldier in Time After Time

**Author's Note:**

> Each chapter will be titled with the relationship featured and each can be read alone. There will be no particular order. Each chapter will have its own warnings that I'll put in the author's notes. (Also, if you really, really hate Dean/Castiel this may not be for you because there will be occasional mentions of their relationship outside of their chapter, but I'll warn for it.) (No chapters will involve incest).

**Author's Notes: It isn't letting me put notes the normal way so until I figure it out, here goes. This chapter's warnings are brief non-explicit mentions of homophobia, semi-public sex. Also, this probably (almost certainly) doesn't fit exactly into 7x12, but I'm guessing y'all are here for the smut not the continuity.**

 

“Sentimental Journey” plays just above the buzzing of the radio static. Besides the fry cook and owner, who has gone to the back kitchen and not come out for quite some time, Dean's alone in the diner.

Dean leans his chin on his hands and stares at the mostly-empty chocolate malt glass, maraschino cherry left at the bottom. He’s never really liked the taste of them, like bad cough syrup.

The door squeals open and Dean turns on instinct toward it. His stomach drops; he tingles under his cheekbones to his lips. It’s the soldier he’d seen in the street earlier, the one he couldn’t help but stare at.

“Can I sit here?” the man has a soft southern accent because _of course he does._ It’s strange, with all the empty seats, to ask to sit directly next to Dean, but Dean doesn’t want to get his hopes up. Still, Dean nods.

The man takes off his hat as he sits and sets it on the counter. He runs his hand over his hair. “I could really go for bacon and eggs. It’s midnight – is that strange?”

“Hey man, anytime is bacon and eggs time. Same for pie.”

The soldier sighs softly, and it’s a masculine sound that makes Dean shiverand grip his hand tightly onto the pants he’d acquired earlier that day. He likes these clothes. The high-waist fit of the trousers, the looseness around his thighs, the cufflinks, the suit jacket, the tie – and especially the fedora, which was sitting on the counter besides his malt drink.

“Pie also sounds good.”

“Don’t get much of that overseas?”

The soldier chuckles. “Nah, not much pie in Normandy.”

“You were in Normandy?”

The soldier’s lips quirk into a frown. “So were a lot of guys. Only us lucky ones came back.”

Dean was happy for the break in the dark conversation when the fry cook arrived to gruffly take the soldier’s order: Bacon and eggs, slice of Strawberry Rhubarb (Dean orders a slice of pecan) and the cook tells both him and Dean he’s closing in an hour.

The radio is now playing “Moonlight Serenade”, and they both sit in a comfortable silence as the sounds of Glenn Miller fill the dimly lit diner. Occasionally Dean steals a glance at the man’s blond hair, his grey eyes, the soft stubble on his upper lip. A few times Dean swears the man is looking back.

The fry cook brings the platter of food and sets it front the soldier. He hands Dean his pecan pie.

“I’m Paul…by the way.”

Dean smiles and takes a bite. “Dean.”

“Dean. That’s a good name.”

As they eat, the two men talk about war, about movies (though Dean is careful not to bring up any that haven’t come out yet), about women…their knees are getting dangerously close. The brown fabric of the soldier’s uniform brushing against Dean.

Dean can’t help but watch the way the fork slides into the man’s mouth – his pink tongue curling around the tines, his lips squeezing, his Adam’s apple dropping as he swallows. Paul is an American dream and one Dean usually wakes himself up from, but it’s 1944, it’s half past midnight, and Dean Winchester has always had a thing for a man in uniform.

Dean casually lets their knees touch. Paul’s back straightens and for a heart-skipping moment Dean thinks the man is going to pull away, call him some homophobic slur and take a swing (wouldn’t be the first time it’s happened) but he presses back, falls into the touch. Dean glances over; their eyes meet. It’s a hot glance, one painted in desire and lust. Dean wants to give into it, wants to fuck with young Frank Sinatra’s voice crooning in the background.

“Wanna pay and get out of here?” Dean growls.

Paul grins, his eyes widening and face flushing. This is a risk for him and Dean knows it. 1944 is a different time, a whole damn different world, but Dean isn’t gonna fuck anything up for this guy, he promises himself, he’s just gonna make them both feel good.

They pay for their meals, grab their hats, and they’re both quickly out the front door.

The streets are absolutely vacant, the air just that perfect chill that makes goosebumps run down Dean’s spine. The stars….they’re in town, but Dean can see stars like he’s never seen them anywhere but deep in the woods. Everything feels so young here, adolescent almost, and it’s seeping into the recklessness he feels under his skin.

“Where do we go?” Paul’s voice is a little shaky.

“There’s no one here. It’s dark. No one can see us. I promise.” But just to be safe, Dean leads Paul away from the diner, behind a dumpster in a pitch black alley. It’s not ideal – it’s too dark to see Paul’s angled, gorgeous features and it smells terrible – Dean wishes he could fuck Paul on the hood of his Impala, parked in a field at noon, but that’s not how things are.

Dean sets his hat on the asphalt, Paul does the same, and then his hands are everywhere on the soldier before he even realizes it. The uniform is rough, hot as hell, but it’s scratchy to the touch. Dean backs Paul against the wall, he’s young probably 24 at most, and eager, soft and hard in all the right ways and places.

“You done this before?” Dean speaks against Paul’s pliant mouth.

“Yeah, back there. Yeah,” is his quiet reply.

Dean cups Paul through his uniform and Paul tosses his head back, groaning.

“Shh. buddy,” Dean whispers as he unbuttons Paul’s pants. “Don’t wanna wake up the whole neighborhood.”

It’s only then Dean realizes he hasn’t kissed Paul, hasn’t had those chapped lips on his own. His fingers trace Paul’s jaw and Dean leans in slowly – he wants to make this good, epic, he wants this man to remember him. Their lips meet and Paul plunges forward, his hands gripping onto Dean’s tie, pulling them together. Dean slips a tongue into Paul’s mouth and lets him suckle at it, then he takes control of the kiss again and it’s all power, finesse, desire, like making love should be – not that that’s what they’re doing, but Dean – Dean with his infinite rules about what it means to be a man – believes in fucking like a real man intent wholly on the pleasure of the other.

Dean pulls his mouth away from Paul’s, kisses across his jaw and down his neck, his hands are spread and press over the uniform as Dean slides to his knees in the alley. He mouths at Paul’s cock through the scratchy fabric, pulling a moan from Paul’s lips. With his teeth, Dean loosens Paul’s belt, licks back the prong holding it in with his tongue, uses his mouth to tear open the button, his teeth to slide down the zipper, his deft thumbs to slide down Paul’s boxers just enough to release a hard, cut cock. Dean runs the stubble of his 5 o clock shower over the sensitive skin, and Paul purrs.

God, Dean is so hard too. He rubs himself quickly through his pants, desperate for a moment of friction. Dean removes a condom from his wallet, tears the packet open and slides it over Paul’s erection with his mouth. Paul bites down on his own hand.

Dean’s good at this. He makes it a rule to be as a good at all the facets of sex as a man could be. He always starts slow, just the tip, massaging it with a swirling tongue, then as he listens to the sounds, the tension of Paul’s body, how he responds, Dean slows it down or speeds it up.

Paul likes it faster, deeper, harder – he can tell – a lot of men do and Dean has no problem giving it to them. Slowly, he takes Paul’s dick as deep as he can in his mouth, feeling the sweet-burn-stretch of his lips around the thickness. Paul thrusts a bit deeper.

“Sorry,” Paul mutters.

It’s fine. Dean can take it and he wants him to know it so he takes him even deeper, all the way down to the blonde curls and then slowly slides back up, spiraling his tongue around Paul’s dick until he pops off.

“Fuck my face,” Dean whispers.

Paul growls and grips the back of Dean’s hair and presses his dick in his mouth again. Dean loves this too – letting go – letting himself be molded into whatever his partner wants, needs. He relaxes his mouth and his jaw, let everything fade except Paul’s pants and the feel of heavy latex-covered flesh on his tongue.

“I want-“ Paul pulls away from Dean.

“You can come, Paul.”

“ _No,”_ he says voice dripping with a desperation that makes Dean’s whole body buzz. “Want you. Inside me.”

Those words wake something up in Dean. It’s primal, wild. Dean gives into it. Dean stands up, kisses Paul, deep and slow, then positions him bent-over with his hands against the wall. “Yeah, just like that,” Dean hisses in his ear.

Dean takes out a small package of lube from his wallet (he’s smart enough to always have it on him just in case) and pours it over his fingers, warming it up, before he presses one finger inside of Paul and watches the lines of Paul’s body become taut and then relax into this touch.

“That’s it, buddy,” Dean says, “Relax.”

Dean adds another finger and another, until he touches something inside Paul that makes him shout – like really shout.

“Shh, man you’re gonna have to be quiet.”

“Cant’-“

“God, I love your sounds, but we can’t here.” Dean twists his fingers and Paul groans.

“Really can’t help it,” he pants.

Dean pulls his hands away from Paul.

“Don’t stop.”

“Hold on, pal.” Dean twists off his own tie, easily pulls it off and coaxes Paul’s mouth open with his fingers. He slides the tie in and wrap it’s twice around his mouth and ties it at the back of his head. It won’t keep him silent, but it will quiet him enough and serve as a reminder.

Dean returns his slick fingers to Paul’s hole and opens it up as Paul murmurs and mutters and curses sweetly around Dean’s tie.

“Ready?” Dean asks, pulling out and softly running a thumb over Paul’s opening.

He nods enthusiastically and Dean grins.

Dean is so, so ready.

He gets another condom and slides it over his achingly hard dick and lets out a shaky breath. Dean’s all about control and precision, but right now he’s trembling a bit, feeling himself start to come apart with desire.

Dean steadies himself as he positions his cock at Paul’s entrance. He kisses against the fabric of Paul’s uniform as he presses inside and _fuck_ the heat, the tightness. It’s so much, almost too much. He slides all the way in and waits. Paul is pushing back, little abortive thrusts, so the time Dean waits is more for him than the other man. He’s got to get his head together so he last more than 10 seconds.

Finally, he does. Dean knows he’s ready and he begins to move, in and out, slow and fast, he knows how to move his hips in delicious circles until he finds the spot that makes Paul arch like wild cat, and he keeps aiming at the spot, pulling away enough to keep the jolts of pleasure intense and unexpected.

Suddenly, Dean’s head is in a strange place. He thinks of this man, who’s hands are on an alley wall and who’s ass is wrapped around Dean’s dick, he thinks about the fear he must live with everyday, the self-hatred, and it’s something Dean knows like he knows his own skin – and he doesn’t feel sorry for Paul, for the hard life he’s got ahead of him, he just feels, he feels how strong the soldier is. Soldier, lover, and Dean wants him to know, just for this moment, this one isolated moment in a million other moments that will all blend together into the mostly meaningless, utterly mortal – he wants Paul to know it matters, this connection _matters._

Dean covers Paul’s back with his own and kisses under his ear. He whispers sweetly into it.

_You’re so good – feel so good._

Dean wants to say his name so Paul knows it couldn’t be just anyone else here. Because it couldn’t be – it has to be this. It _is_ this, and so many little details came together in both their lives to them here together, tonight.

 _Paul,_ he says, _Paul, you’re fantastic._

“Dean,” it’s a muffled _Dean_ because of the tie, but it’s clearly, completely, a Dean. Dean removes the tie.

“I wanna hear you. Hear everything.” It’s not a moment that’s meant to be breathed into the silence and washed away. It’s a moment to be shouted, a moment to declare.

When his mouth is freed, Paul is muttering Dean’s name and _fuck, harder, more, please, make me feel it, want to feel it tomorrow._

Dean shoves in harder, fucks him, takes him with all the pounding lust and want that’s built up in his bones. He wraps his hand around Paul’s dick, pushing the condom off so it’s just the skin of Dean’s hand against Paul’s straining cock.

“God, yes, Dean, fuck, so close.”

“Me too, Paul. Me too.”

Dean slides his hand a few more times, squeezing and thrusting in a matching rhythm. Paul shouts, really shouts, and it’s cathartic as Paul shoots hot and sticky over Dean’s fingers. The gates open on his own pleasure and Dean comes too – hot, dizzying tingles radiating through his body as he thrusts shallowly again and again, emptying into the condom, into Paul.

Dean takes a breath, kisses Paul on the back and slides out as slow and gentle as he can manage. Dean tosses out the condom and pulls on his own pants back on. Paul’s doing the same. Dean’s tie is on the ground and nobody moves to pick up the evidence, that marks this spot as their’’s, as something real.

It’s still very dark, but his eyes have adjusted enough that Dean can see the smile on Paul’s face. Dean steps closer, cups Paul’s face and kisses him. It’s soft and sweet, with a barely-there hint of tongue.

“I’ve gotta go,” Dean whispers apologetically.

“Me too,” Paul leans in and kisses him softly.

Dean steps away from the soldier’s touch, puts his fedora back on and walks out of the alley without looking back.


	2. Dean/Crowley

**Summary for the Chapter:**

> Dean/Crowley. Demon!Dean has angry sex with Crowley, but Crowley thinks it's more than it is.

**Notes for the Chapter:**

> Warnings: Angry sex, rough sex. Mentions of past Dean/Castiel. Demon!Dean Season 10

His hands – his hands are warm, the good kind of warm, not the hell kind of warm – warm like a hearth, like a campfire, like human things Crowley can hardly remember now. Dean isn’t technically human, but even with black eyes he is more human than most living, breathing people are. That’s, well, that’s remarkable.

Crowley isn’t sure how he got here. Well, it has something to do with Jose Cuervo and Angry Orchard and Southern Comfort, but it’s more than that, isn’t it? With the way Dean’s lips suck a bruise, an impossible bruise, into soft spot between Crowley’s neck and collarbone, it has to be more than chemical?

…

It hurts – it _fucking_ hurts – and it shouldn’t feel like anything, but Dean is so damn numb that it hurts, and he’s reaching. He’s reach, reach, reaching for anything. For fire, for ice, for poison, anything to take the edge off the numbness. If that means he has to lie on top of Crowley, push their bodies together, bite into his skin, peel him apart, then that’s what it means.

. . .

Crowley feels – and normally, he’d shy away from the feeling, but how do you shy away from Dean Winchester? This man, the strength of his arms as he pulls off Crowley’s clothes, untamed, monstrously beautiful, this man with a thousand years behind eyes not even half a century old. His soul, his _soul,_ still glows with a righteousness that would put an angel’s grace to shame. No wonder Castiel touched it in hell and never came back from it- you don’t come back from this.

Crowley mindlessly reaches to take off Dean’s clothing and Dean lets him. Crowley reaches to slide off his own socks.

“Don’t,” Dean bites and then Dean’s kissing him. When was the last time somebody did that? He’s fucked and been fucked, but kissed, for anything besides a crossroads deal? No. Who the fuck kisses the king of Hell anyway, and kisses him like this? Like Crowley matters, like Dean wants the press of their tongues together, like he reels from it, like he feeds off it?

. . .

Dean isn’t here. Not really. His body, the one that’s touching Crowley, kissing him like this, is just the echo of a dead man. Dean, human Dean, real Dean, he’s in a motel, in Rexford. He’s got a tipsy Castiel, wearing nothing but his socks, panting on top of him and the world is singing around Dean like a chorus.

A part of Dean thinks that he lost his mind in that motel room. That when Cas came inside him, Dean lost his mind, and this whole last year has just been an elaborate hallucination he’s having in a psychiatric ward. Dean’s not sure what’s true – not sure what reality is better.

. . .

Dean shoves his fingers in Crowley’s mouth and Crowley sucks on them. Dean slides them out and then moves them between Crowley’s legs, pushing his knees up.

“Are you going to fuck me, Dean?”

Dean doesn’t reply with words. He just shoves his middle and ring finger deep inside Crowley. It doesn’t hurt – Crowley is a demon for God’s sake and can get thrown across the room and get back up – but it isn’t gentle, not that Crowley wants gentle. He likes it like this – likes that Dean is so out-of-control for him, so desperately wanting him, that he can’t even wait.

“Yes, Squirrel, just. Like. That.” Crowley is thrusting back against Dean’s fingers and this small part of him wants to take a picture of this and send it to Sam, hell send it to Cas, let them know he’s won, that Dean picked him and he picks Dean, but he doesn’t because this is between them –and it’s hot, needy and violent in a way, but it’s special, it’s private and Crowley will fold this moment into himself and keep it.

Suddenly, Dean’s fingers are no longer inside him and Dean slides up his body, naked and sweaty. Crowley touches the anti-possession tattoo on his chest, but then it’s out of his reach and Dean is pressing his cock against Crowley’s mouth and Crowley opens to it easily.

“Suck me,” Dean commands. Crowley has no problem obliging him – and he can’t even make a sarcastic retort because Dean’s cock is filling up his mouth.

It’s an unexpected thought, as Crowley tongues the slit of Dean’s dick and hears him growl, Crowley _loves_ this, wants to keep it, wants to keep Dean, keep them, because he feels it, this nameless, new emotion, like something sweet and warm between his ribs. Crowley doesn’t know what it is or what it means. He just knows he never wants to stop feeling it.

. . .

There it is. Dean feels something other than numbness and it’s anger. It’s heated rage that burns his skin like acid and he can take it out here, he can give into this anger, with Crowley’s mouth around his dick. Dean can tell Crowley how he feels right now.

Dean can tell Crowley how much he hates him.

. . .

Dean pulls out of Crowley’s mouth and Crowley whines, missing the weight against his tongue. He flips Crowley onto his stomach with power that makes him shiver, makes him want to fall apart and open up and be opened up by Dean. Dean who is pulling his ass cheeks apart.

“Tell me to stop,” Dean growls lowly, his breath a hot cloud that travels across Crowley’s spine.

“Fuck me,” Crowley growls. “Split me open on that huge cock of yours.”

Dean doesn’t go slowly, _can’t,_ Crowley thinks, because that’s just them. That’s just how hot, how compelling this thing is between them. It’s a freight train that can’t. That _won’t_ be stopped.

Dean bottoms out and doesn’t give Crowley a moment to take it in. Dean grips Crowley’s hair and holds onto it, yanks it back, and then pounds into him. Just slams into him over and over and over. Crowley’s head is spinning, spiraling out of gravity, beyond the reach of his fingertips. Having Dean inside him like this, stretching him to his limits, he’s never wanted anything the way he wants this.

. . .

_Fuck, anger, harder, hate._

_Fuck him._

_It’s his fault. His fault this mark is on my arm, that my eyes are black…_

_That I’m a demon._

_Not his fault – your fault._

_You’re as worthless as he is._

. . .

Dean is so desperate for Crowley, that he forgets to touch him, so Crowley touches himself. Dean ramming inside of him is so good, but it’s not enough to bring him all the way there and he can feeling Dean shaking around him, feel that Dean is getting close and suddenly, he is there, coming inside Crowley with shot after shot of a heat that coats him on the inside.

Marked by the righteous man, corrupted by Crowley’s own hands into something dark and beautiful.

That’s enough and Crowley’s comes all over the motel sheets.

Dean pulls out of Crowley quickly and slides off the bed. Crowley’s face is pressed into the pillow, completely wrecked in a way only Dean Winchester could ever do to him.

“I’m goin’ to the bar for a drink.” Dean dresses quickly.

“Right behind you, jerk, “ Crowley says and smiles to himself, as he sits up in bed.

There’s a pause.

“Bitch.”


	3. Dean/Dildo

**Summary for the Chapter:**

> While John is away and Sam at college, Dean has his first time with a dildo.

**Notes for the Chapter:**

> Dean/Dildo. Tags and Warnings: Mentions of homophobia and sexist terms. Sex toys - dildo. Masturbation.

Dean shakes as he lies on the motel bed. The cheap sheets scratch at his back as he moves, writhing against them. No one else is here. The door is locked and bolted; the TV is on, playing a _Gunsmoke_ rerun. Dean couldn’t do this in silence. It would feel like someone could hear even though they can’t.

He squeezes his hand up and down his dick, up and down, fast, slow, twist, up and down, fast…slow…twist. Just the way he likes it. The scars and callouses on his palms rub roughly against the velvet smooth skin of his leaking cock, making him delirious. Up and down, fast, slow, fast, slow, twist, twist, twist.

“Uh, God, yes!” He growls.

He needs it. Wants it.

His mouth is open and dry from gasping. Dean has to wreck himself first, tear himself to pieces because if he isn’t falling apart he’ll never be able to manage this no matter how much he aches for it.

Trembling, Dean reaches to the nightstand and picks up a small bottle of lube. He pours it on his fingers. It smells like peppermint and when he pours it on his skin it warms. First, he uses it on his dick, sliding his hand up

…down

up…

…down

fast,

…slow…

twist,

twist,

The pleasure sizzles on his spine and spreads out across his body. Dad isn’t here – Sammy’s in college. Dean’s alone, really, really alone and he takes advantage of it. Taking his time with himself, making sure he feels it, that he _feels_ this.

Biting down on the inside of his cheek, Dean slips his hand even lower, pouring a little more peppermint lube on his fingers and his balls. He fondles them for a moment, rolling them in his hand, something he loves but rarely does. Dean groans, unable, unwilling to stop. Courage and desire mix just enough for Dean to keep moving his hand, down, down, down until it’s there – at his entrance.

Dean licks his lips and lets out a shaky breath. His fingers are slick enough and when he presses it against his hole, it gives willingly, though tightly, to the touch. Dean’s eyes widen as the tip of his pointer fingers slips inside. Breathing shotgun breaths, Dean pushes that finger even deeper, reveling in the hot, tight stretch of himself. Dean slides his finger just a little bit back out and then pushes it back in.

“Ahh!”

He does it again.

“ _Oh God.”_

And one more time.

“Mmm.”

Before pushing his finger in as far as it can go.

It’s a good burn and Dean is pleasantly surprised. It doesn’t hurt nearly as much as he thought it would. It just feels tight, full, and he instinctively clinches around the touch. Dean pours on a little more lube and works in a second finger, just the same as he did the first, only a little faster, hot with an enthusiasm from how good this is…how much easier than he thought it would be.

Dean is three fingers in before he even realizes how much he’s stretched, how tight and full and wet. He’s sliding them in and out, twisting, and he touches something that shoots sparks through his body like lit gunpowder. His other hand still strokes his dick.

Dean screams, half from pleasure and half from shock. It’s his prostate. Has to be. He does it again and again and again until his whole body is ablaze with the impossible, overwhelming sensation.

It’s time and he knows it. Dean slips his fingers out of himself. He skims the pad of his thumb over his hole. It’s slick, open, wet, puffy and so, so sensitive. He runs his thumb over it a few more time, shutting his eyes, pushing out everything else but the tingling touch.

He reaches over to the nightstand and finally touches it. It’s a deep blue silicone, 7 inches long, no wider than his own dick. He picks it up and pours peppermint lube all over it, until it’s slick and ready, just waiting for him. Dean takes his time, building his nerves, as he positions the dildo at his entrance and lets the cold plastic press against that raw skin.

He waits…

Waits…

Waits…

And then slowly inch by inch he begins to press the silicone dick into his body. Dean’s mouth is wide open in a silent scream as he’s stretched farther than ever, so far, for a moment, he wonders if he can’t do this, if he should stop, not just for the physical burn, which isn’t really all that bad, but it’s overwhelming mentally, makes Dean face what he doesn’t want to face, what he tried not to for so long, despite what he’s done. Dean’s being fucked – not by a man – but still _fucked_ and he loves it, wants it. Right now, he’d beg for it if he had to.

Dad would probably call him pathetic, a girl, a pussy…he’d call him worse if he knew, but he doesn’t _have_ to know. This is for Dean and nobody else.

Before Dean knows it, the dildo is all the way inside him, pushed deep all the way in to the flared base. He breaths heavily, watching his chest rise and fall as he just lets his body get used to the new feeling, the new stretch, the new fullness. He rubs his hand softly up and down his dick, caressing the skin, thumbing the slit. He wipes up a few droplets of pre-come and then rubs it over his left nipple. He hisses as he rubs and pinches at the flesh, jolting himself with pleasure.

Finally, Dean feels ready enough to pull the dildo out a little and then push it back in, _fuck it_ back in. It’s easy from here to pick up the pace, in and out, in and out, slow, fast, slow. He hasn’t yet found that incredible spot with his finger not until he…

And there it is.

Dean shouts a gravely, hoarse shout that scratches at his throat, again and again, as he keep shouting each and every time he pounds against his prostate.

God, he loves being fucked.

He can’t stop himself from imagining that it’s not cold silicone inside him but instead it’s the fleshy, hot dick of some muscled bartender with big arms and tats and _God_ a short beard that scratches and burns his skin. Dean pulls his knees back, imagining that he’s being fucked hard, legs up, and just taking it, taking it like goddamn champ.

“Give it to me,” Dean mutters under his breath. “Take it. Give it to me. Come on. Come on.”

Dean keeps slamming the dildo into himself over and over, pumping faster and faster. He can feel it burning in his legs, he’s so full, so tight, so close. God, it’s just so much and Dean can’t stop it anymore, doesn’t want to.

He imagines that fantasy bartender, leaning down and kissing him, fucking a tongue into Dean’s mouth, as he bottoms out deep in Dean’s ass. He imagines a scratchy, rough male very male voice growling, “Come. Come on my dick.”

And he does.

He clinches tight around the silicone, like a cock he wants to milk, his own dick spitting and spewing long sticky stripes of semen across his chest, onto his chin, one after the other like it’s drying out his whole body.

Dean lets out a long breath and then sucks it in deeply and blows it out again. He grins, enjoying the sleepy afterglow, his ass still fantastically full, his cock still sticky and half-erect. Dean feels good, glowing.

And then his phone rings. It’s a number he doesn’t recognize.

“Hello?” he answers without thinking, his voice still fucked-out.

“Dean, it’s me.”

_Shit. Dad._


	4. Dean/Victor (sub!dean)

**Summary for the Chapter:**

> Never having done it before, Dean decides to have an experience as Dean's sub.

**Notes for the Chapter:**

> Dean/Victor. BDSM. Consent. sub!dean. spanking. handcuffs as restraints. dirty talk.

“Are you sure about this?” Victor asks as he runs his hand over Dean’s hip. Dean swallows. A blush heats his cheeks. If he wants out, this is the time to stay it.

 

_“I’ll stop whenever- the moment you want. Just say the word. You’re really the one in control here.”_

That’s what Victor had said so of course he could stop at anytime, but this, this would be the best time to do it if he wanted to do it… before…

Dean doesn’t want Victor to stop. He’s sure of that.

He nods.

“Take off your clothes,” Victor says.

Dean moves his hands to the hem of his shirt and then stops.

“Dean, now.”

“No.” That’s not the word to stop this, Dean knows that, Victor knows that. This is something else.

 

_“What if I want to fight?”_

_“Fight? Physically.”_

_Dean shook his head. “Uh, no, not really. Just hesitate, fight you on it.”_

_“You’d like that?” Victor raised an eyebrow._

_Dean let out a shaky breath and nodded._

 

Victor grabs Dean’s, not painfully, but tight. “Take. Your. Clothes. Off.”

“All of them?”

“Yes. Do it now.” Dean frowns, like he doesn’t want to take the orders, even though he really does – and he starts to peel the shirt off and over his head. Victor is just a few inches from Dean, not touching, but watching intently.

Piece by piece, he bears his tan, freckled skin to Victor, who’s lips are curled into a small smile.

“You’re beautiful, Dean.”

He normally hates when people call him beautiful, or he’s normally supposed to hate it when people call him beautiful, but tonight he revels in it.

Dean’s eyes cast down to Victor’s pants where there’s a very obvious bulge.

“Yeah, Dean. You make me hard.”

“Did I always?”

Victor laughs. “You mean when I thought you were a murderer?”

“Yeah?”

“I thought you were a sexy murderer. You’d find, unfortunately, those things aren’t always mutually exclusive.” Victor rakes his fingers through Dean’s hair. “You ready?”

Dean’s shaky but he nods.

Victor reaches into his pocket and pulls out a pair of handcuffs. This is one of the first things Dean asked for when he and Victor decided to try this together. Gently, Victor puts Dean’s hands behind his back and handcuffs him. Dean is already crazy horny just from this, just from imagining.

“Damn, Dean.” Victor backs away and sits down on the edge of his bed and smoothing his hands over the suede grey comforter.

“Come here, beautiful.”

Dean’s suddenly frozen. He’s ready and not at the same time. He’s unbelievably hard. His cock is red and leaking; Victor is staring at it and this _was_ Dean’s idea. Dean steels himself and steps forward.

“Bend over my knees,” Victor says and Dean has trouble complying so Victor manhandles him down and he appreciates it. Victors hands slide all over Dean’s exposed skin, underneath his locked hands, on them, running around the border of the cold metal cuffs.

“God, kid, you have so many scars. Too many.”

Dean stiffens. Nobody’s complained about it before. Women usually love it. He didn’t know he was that marred.

“You’re gorgeous. Don’t get me wrong, just, you’re too young to be hurt like that – I don’t know if I should.”

Wait, he’s not going to. No, he has to.

“ _Please.”_

“Dean, I-“

“You’ll stop if I say the word, right?”

“Of course,” Victor replies without any hesitation.

“I want this – I need – I need to be able to control the pain for once.”

“Okay, okay,” Victor smoothes his hand over Dean’s ass. Spreads his cheeks and plays with Dean’s pucker a bit, which makes Dean shiver.

“Victor.”

“Sir,” Victor corrects.

“Sir.”

Before Dean knows what’s happening, Victor’s hand makes hard contact with his ass, the slap ringing through the room. Dean shouts and Victor does it again. It actually really fucking hurt, but Dean doesn’t really mind at the same time.

 

_“What do you want me to say when I spank you?”_

_“What do you mean?”_

_“Some people like me to count, some like me to insult them, tell them why I’m punishing them. What would you like?”_

_“I’d rather have you count than…”_

_“There are other options. I can also just stay quiet.”_

_“I don’t know. I just…”_

_“There’s also, I can tell you how strong you are, how good you are, taking it for me?”_

_Dean looks up at Victor, “Really?”_

Victor keeps spanking him; Dean keeps shouting, groaning, hissing at the contact. His dick was already swollen and red and heavy, bouncing against Victor’s clothed thigh as Dean’s face pressed into the mattress.

“Shit, Dean. God, you’re good, so good. So strong. I’m pushing you so far and you just you take it.” _Slap._ “You’re ass is so red, and you just… so strong, beautiful, so damn strong. I love that you get hard just from this. I bet you could blow your load just from being spanked.”

Dean’s mind kind of drifts, so he’s floating in the pain, the pain isn’t really pain anymore, just this sexual, heady sting that he loves. He’s not sure he’ll ever ask Victor to stop, but he just starts slowing on his own. They’d had a plan about this and Dean’s not following through on his end.

 

_“Can you, can you beg me to stop?” It’s time for Victor make a request._

_“Yeah, yeah, I think I’d like that.”_

Right, right, Dean pulls himself back into his own head no matter how good it feels to be floating out there. This is a give and take situation.

“Stop, sir. Please, it’s hurts. Please.” Begging doesn’t necessarily sound right on Dean’s lips, so foreign, but he’s not being judged here – no matter how much his burning blush tells him over wise.

“A few more, Dean.” This time, Victor slaps Dean between his ass cheeks, right on his entrance. Dean cries out. Victor does it a few more times. Suddenly, Victor’s slick (where the hell did the lube come from?) fingers are pressing inside him, making him full and needy, twisting to hit his prostate and send jolts of pleasure to every inch of his body.

“Please, please. Sir. Stop, stop. I need to you.” Dean is sobbing and he can hardly believe himself. He loves this and can’t decide if that makes him hate himself.

Victor keeps fingering Dean until Victor is three fingers deep into Dean and fucking hard. Victor jacks Dean a few times and Dean comes all over Victor’s pants with a broken sob, squeezing around Victor’s fingers. When Dean comes down from the dizzying high, Victor slowly slips each finger out one at a time.

“Shh, shh, baby.” Victor strokes the raw flesh of Dean’s ass. “We’re all done. You did so good.” Victor pulls Dean into a sitting position and tucks his head into his neck. Dean trembles against him as Victor kisses his neck. This feels surreal, in a good way, like Dean is floating outside of himself and looking down on a fond memory.

Dean slides out of Victor’s arms and falls between his legs.

“You don’t need-“

“Want to. Please…sir.” Dean widens his eyes and looks up at Victor as innocently as he can. Victor smiles down at him, chuckles softly and opens up his pants, pulling out his dick.

This is the first time Dean has seen it. It’s long, narrow in a nice way and uncut. Dean whines and finds he doesn’t have any control over the sound, the sound that makes Victor’s cock twitch.

Victor strokes it a few times and then presses it to Dean’s lips, pushing inside, slowly but deep.

Dean clamps down a bit, afraid to take it all the way in.

“You’re so good, Dean. I bet you can do even more for me. Can’t you, beautiful?”

Dean wants to live up to what Victor thinks of him so he relaxes and lets Victor press in even deeper until Victor’s dick presses on the soft palette of Dean’s throat.

“Squeeze my calf if it’s too much,” Victor says, sounding wrecked.

Dean does his best to nod with Victor’s hand still forcing Dean’s mouth down on his cock, his nose pressed into the black hair around the base of his dick.

“I’m close, Dean,” Victor mutters. “You already had me so close. Just from touching you, from watching you desperate, watching you come.”

Dean wants Victor to come down his throat. Victor is clean and so is Dean. They would’ve used a condom if they were to actually fuck and Dean is already breaking a rule of his by blowing without a condom, but he’s broken a lot of rules today.

Dean’s ready for the salty pulse in his mouth, but instead Victor pulls out, jacks himself a few times and comes all over Dean’s face, hot and sticky. Victor takes a few moments to breathe and then slides down on the floor with Dean and kisses him fast and messy and deep, his tongue licking away the semen on the Dean’s face.

“Thank you, Dean. Thank you. So glad I arrested you,” he mutters against Dean’s ear.

“Yeah,” Dean laughs. “Worse things have happened.”


End file.
